(Pictured above, Neal and I on our first New Years Eve together when he accidentally told me he loved me after 4 months of dating. Obviously I loved him too–the look on my face!)
While this post was published MANY years back now, it has become a bit of a tradition to re-post it around Valentine’s Day. I always get asked the story of how we met, and with so many new faces reading the blog each year, I can’t think of a better post to re-publish in the spirit of true love!
Do you believe in fate? We definitely do. You’ll see why in a second!
I thought it would be fun for both Neal and me to share the story of how we met completely independently of one another. And I was nervous/crying/laughing all at once reading his responses for the first time. I’m such a sap. I hope you enjoy this post as much as we enjoyed reading and writing it.
Read on for both sides of the story ❤️
Jess on how they met:
It was June of 2010, I had just moved to Chicago after graduating at IU and was getting ready to start my first job at a staffing company as a “recruiter” (but not like, a real recruiting job, it was basically a 70 hours per week “sales” job that turned over recent grads like a factory). This was something totally unrelated to what I had received my degree in–Journalism–and far from what I wanted to be doing (Advertising), but it was a job with a paycheck, none-the-less. (2010 was not an easy market to get a job in!)
There was an office party at a “Whirlyball” center (if you don’t know what that is, it’s kind of like basketball in go-karts, which is essentially my very worst nightmare).
Luckily, there was a bar.
Actually, I hadn’t started work yet (that would be the following week) so I literally knew nobody other than a guy friend I had attended IU with, who also happened to work there.
I walked in and was greeted by my new manager, who then introduced me to Neal, who would be my partner. I have such a vivid memory of me standing at the bar looking at him like, “Hm. Wow. Okay, this is going to be interesting.”
Neal on how they met:
We met at Whirlyball! This was, of course, an office event for our new “careers”–AKA an entry level job most people quit after a few months. (We would come to find this out quite quickly after this point.)
It was a summer day in 2010. I had already started work but Jess was the brand new girl that was going to start on my team the following week. I found this situation to be both exciting and nerve-wracking.
But as our boss (who was 27 at the time, yet seemed so old and wise) explained, she had a boyfriend and I had a girlfriend so it would be easy. I bought that until I actually saw Jess. More on that later.
The first day we met and hung out unwound in a predictable fashion.
The median age in our office (so funny thinking about how quickly people bailed on that job) was about 24. Highly competitive Whirlyball games, too much drinking, and everyone feeling SO grown up at our first work social gathering.
Come to think of it, that was the first time I was in a bar where everyone around me was actually of legal drinking age. I spent the day trying to find the balance between getting to know my new teammate Jess, not making it look like I was trying to get to know my new teammate Jess too well/appear to be hitting on her, and getting to know the rest of the people in our office in a more casual setting. The whole day/night was a ton of fun.
Jess’ first impression:
Very first thought:
This kid is totally the popular, hot jock I would’ve been terrified to talk to in high school. AND I have to work with him. THIS IS TERRIFYING. But god, he’s cute.
2nd thought immediately after:
Crap [insert boyfriend at the time’s name] is not going to be happy when he finds out I have to spend all day every day sitting across from perfect athletic frat boy. [Note: I was right. That didn’t go over well. In hindsight–obviously. Can you blame him?]
It was like this immediate, striking chemistry I’d never experienced immediately meeting another person. We instantly became friends. He also was super nice to me and helped me not look like a total athletically challenged idiot attempting to play Whirlyball with my new co-workers. I couldn’t even figure out how to make the cart go the right way, much less drive and throw a freaking ball into a hoop at the same time. (Also, keep in mind, this office was 95% competitive males. It was like my horror gym days coming back to haunt me from childhood.)
There was a point where he could have made a shot, but he totally set me up for it and tossed me the ball to make it instead. I just remember being shocked that cute competitive athlete boy had been so considerate. (Remember, up until this point, I was very scared and intimidated by cute competitive athlete boys of any kind, and I totally thought they were all a-holes.)
Neal’s first impression:
I’ll never forget the way she looked at me the first time we met. Never. I know I had the exact same look in my eyes. Something that said “I’m going to sit directly across from HER for 12 hours a day?” It was a combined feeling of pure joy and fear. We were both dating other people, rather seriously. Both dating great people I might add, which made things easy and hard at the same time. I’m getting ahead of myself, but I swear every one of those thoughts went through my head the first time I laid eyes on Jess.
She has this amazing smile, and a kind, cute, approachable gaze.
She’s striking in every way. Beautiful would be an understatement. She also handles herself well in this brand-new crowd. Everyone seems to like her without knowing anything about her, and I am certainly one of those people. She’s cute, friendly, and can’t drive the Whirlyball cart for shit. I decide to let this slide (and continue to let her poor driving skills slide to this very day). She also has this distinct laugh. I’m not sure if I should love it or hate it.
Overall, it takes me about 1 second to realize that I really like Jess. A lot.
I try to convince my brain that I really like her just as a friend and a work teammate, but looking back on it, I always knew. When we said goodbye after that first day I couldn’t wait to see her again, even if that meant seeing her at 7 am on a Monday at a miserable entry-level job.
Jess on what happened from there:
We became really good friends and spent at least 12 hours every day working together. We went to lunch together, we would grab dinner together to kill time and wait for traffic to die down after work. And we would text each other late about work. (Since we would work for 12 hours at the office and then work more at home.)
He was the best friend and teammate.
He was always encouraging, would go out of his way to help me, and always did whatever he could to make me shine at work. We would talk on the phone at night for work-related things and then end up talking for another hour about something completely random.
I totally had a huge crush on him, but I wouldn’t let my mind go there. I was dating a great guy at the time, and totally thought we’d end up getting married, and that was that.
Then, Neal told me he was leaving to go work at the Chicago Board of Trade.
I was devastated.
On his last day we went out for drinks with some other coworker friends and then I literally cried my eyes out in the parking lot saying goodbye to him. And also cried the entire way home. And cried myself to sleep.
Now, just to let you know–I’m not a crier. (Unless I see an emotional commercial on TV involving a dog or I’m watching a sad movie.) Real life though? Nope. Hardly ever. I think I’ve gotten more emotional over the years, but back then, I was definitely not someone I would describe as emotional. So this was a big deal for me.
The next day the director called me into her office and asked if I was okay. [Might this be a sign you’re in love with someone?] I will never forget the first day after he quit and the horrible empty void I felt without him.
Still though, I was in complete denial that I had feelings for him as more than friends.
He then started his new job and we kept in touch loosely and saw each other (as friends!) a few times over the next two years. I remember we randomly met up for drinks maybe 6 months after moving jobs. And I had finally found a new job at an ad agency (yay!) and I had to run errands downtown, which was right by his work. I remember seeing him from down the street and sprinting to hug him, jumping ON him, Romcom movie style, when I got there. (Who does this to a guy they aren’t dating, who also has a girlfriend? 🤣)
My college boyfriend and I eventually parted way maybe six months to a year later, and I remember laying in my bed one night thinking “I wonder who I will end up with. What if I’ve already met them?” I did a mental run through of all the guys I had met in my life, and the only one I could think of “potentially ending up with” was Neal.
Neal on what happened from there:
We became really good friends. (No trashy office romance saga here.) Our jobs sucked, but we took them seriously. We worked hard and were actually a damn good team. We complemented one another well, pushed each other, and commiserated via text when it was 9 or 10 PM and we were both at home working on call sheets for the next day.
After 5 months or so I took a job on the trading floor in Chicago.
I did this for a number of reasons.
1. I had a finance degree and needed to get my foot in the door somewhere.
2. I was clearly falling for Jess, and I felt like I had to put some distance between us. Not surprisingly, both of our significant others at the time were less than pleased that Jess and I had become such good friends.
On my last day, Jess cried when we said goodbye. It killed me to see her cry. I remember thinking, “I don’t ever want her to cry, but I would love to be the one that gets to take care of her when she’s sad.” I knew she was upset because her work teammate that understood the grind of the job was leaving, but I did think tears were a bit extreme for a work goodbye. I always tried to tell myself “She doesn’t like you. Forget about this. You’re stupid for wanting more and could sabotage your friendship.” After that night though, I realized maybe I wasn’t wrong.
Maybe she felt the same way.
Naturally, this is never how things work. We entered a period of years (yes TWO YEARS) where we stayed in touch via text, and then maybe I would go off the grid for months at a time. I wrestled with a college relationship that had not transitioned well into the “real world.” She was single for a year plus, and seemed perfectly content on her own. I remember hoping that I might bump into her at a bar or at the beach with such frequency. How do you think about someone that you haven’t even seen in the flesh in months (or maybe over a year?) so consistently? In time my college relationship ran its course. I didn’t wait very long (a few months) to finally go after the girl of my dreams that had been so close yet so far from me for 3+ years.
Jess on when they actually started dating:
Not until two (I think it was two?) years later. We had both eventually broken things off with our college significant others. So we started talking regularly again and he kept pestering me to hang out but I kept declining his offers. (I am nobody’s rebound girl!) We grabbed drinks one night and stayed out WAY too late. I let him sleep over, but made him sleep on the couch. 😂
My roommates (who always knew I was secretly in love with him) still joke about waking up the next and scolding me, “Jessica. Who is the shirtless boy on the couch? Is that Neal Loftus? TELL ME YOU DID NOT MAKE NEAL LOFTUS SLEEP ON THE COUCH.”
But I wanted to make sure he was for real, so things moved pretty slowly.
We had inside jokes about going on dates but joke dates—like at Church’s Chicken (a fast-food fried chicken chain) or “Steak night Wednesdays at the Pink Monkey” (YES that is a strip club, and YES it was a joke.)
Then I woke up early on a Saturday morning to a call from him. “Get dressed. We’re going to brunch.” (Fine, I’ll let you buy me breakfast.)
We went to brunch that morning, had way too much champagne, and spent the entire following 48 hours together.
I guess you could say the rest was history.
And here’s where the fate part comes in–I often find myself looking around our condo thinking “Wow. I live in Chicago (CHICAGO?) with this incredible person I never would’ve dreamed in one million years I could end up with. Just thinking about the chain of events that had to happen to lead me to this person is mind-boggling.
I graduated high school in Arizona. I was dying to go to Miami of Ohio for school, where my older best friend went. But for reasons [which STILL BOTHER ME] to this day, I didn’t get in. (I had really good grades, I promise.) Heartbroken, my mom’s friend suggested we look at Indiana. I loved it immediately and decided it was the school for me on the spot, despite not knowing a soul. Most of my friends I made at IU happened to be from Chicago. One thing lead to another, when graduation came, I wanted to move there.
Had I attended any other school, I doubt I would’ve ended up in Chicago.
Before attending Indiana, I lumped Chicago in the “random Midwestern city” that could be interchangeable with Detroit and Minneapolis. (Weren’t they all the same?) I was a West Coast girl, I didn’t know better.
Then came time to get a job. I interviewed and received offers from multiple companies, but for some reason, had a gut feeling to take the one job in the suburbs. I even remember telling the CEO who offered me the job at another company, “Sorry, I’ve decided to accept another offer.” He asked where, and when I told him–he laughed. HE LAUGHED.
IT WAS THAT BIZARRE.
But that’s not all–upon receiving that job, I could have been placed in one of the four Chicagoland offices, and Neal and I would’ve never met. That many minute details had to fall into place in order to meet.
Neal on when they actually started dating:
Well she wouldn’t go on a real date with me of course. She was very content on her own and very cautious of being a “rebound.” How could I blame her? I had come out of a three year relationship a few months earlier. But I knew this could be real. And I never once thought “let’s give this a shot, maybe a couple dates, see what happens.”
I knew, and I mean I knew that we were going to not just work, but that we were going to be the damn Dream Team. This wasn’t some little fling from my perspective. The universe had opened up, and this was my opportunity to earn everything I had ever wanted in another person. I was intent on not f*cking this up, and I still maintain that rather blunt mentality today.
The statistical chances of Jess and I ever meeting at all are staggeringly low.
She was born in a little town outside Portland, grew up in Scottsdale, decided she wanted to go to college in the Midwest, moved to Chicago for a job, took the job that required she drive 45-60 minutes every morning instead of taking the El downtown, and from there wound up not only working in the same office as me, but on the same damn team. That, ladies and gentlemen just does not add up. So with that in mind, I was intent on at least getting her to meet me for some sort of a date. She dodged me, told me I should “just enjoy being single”, but I persisted. I’m a grinder by nature, and maybe I just wore her down 🙂
I finally convinced her to meet me for brunch on a Saturday morning. It was September 15, 2012.
As I walked out of my condo building I met Derrick Rose (This was the Chicago Bulls star player at the time) who happened to be sitting in his Rolls Royce while he waited to pick up some friends. I knew it was going to be a good day. Jess and I walked to Zella’s (many will remember Zella’s, which likely played a significant role in your twenties if you lived in Chicago during that time) together and feasted on a brunch of bottomless mimosas and about 2 bites of food each. We talked for hours. This did not feel like a first date at all, it felt like I was catching up with someone who already knew me on a much deeper level. We left the bar holding hands and have been inseparable ever since. Looking back, it felt like a dream.
That first date turned out to be a 24 hour affair.
Not like that, but we did fall accidentally asleep once the mimosas got the best of us. I woke up the next day and never wanted to leave her side.
Jess on when she realized she loved him:
Thinking back, tip off #1 was crying on his shoulder in the parking lot on his last day of work. But obviously I didn’t know it then.
I realized I was totally in love with him was when I was coming home from Thanksgiving in Milwaukee (I had spent it with my roommate, Kate’s family, as I did for quite a few years.) Kate had stayed behind for a doctor’s appointment, and I took the train home. Neal met me, and we got in a cab to go back to my place, stopping at the grocery store to pick up some beer. I remember thinking, “This is the best day ever. I’ve never been so happy to be in a disgusting cab on the way to a grocery store.” I don’t what it was about it, it just hit me.
This was, you know, like 2 months into dating. We didn’t actually say it to one another until the following February. (Although he accidentally told me he loved me on our first New Years Eve together–pictured above. P.S. How heinous were my bangs?)
Neal on when he realized he loved her:
To be honest, I always knew. Some moments, lessons, or realizations occur suddenly. This was not one of those moments. I caught myself nearly saying the words wayyy earlier than most couples would be comfortable using the L word. But I really knew it. And I still do. And I always will. Happy Valentine’s Day.
Want more of our story? See the story behind our wedding rings & why we had a church ceremony before our big wedding.